(1S,6R)-6-hydroxy-5-methylidene-1-[(1R,2S)-1,2,3-trihydroxy-2-methylpropyl]-2-oxa-7,9-diazabicyclo[4.2.2]decane-8,10-dione

Base Information

• Chemical Name: (1S,6R)-6-hydroxy-5-methylidene-1-[(1R,2S)-1,2,3-trihydroxy-2-methylpropyl]-2-oxa-7,9-diazabicyclo[4.2.2]decane-8,10-dione
• CAS No.: 38129-37-2
• Molecular Formula: C12H18N2O7
• Molecular Weight: 302.284
• European Community (EC) Number: 253-795-3
• DSSTox Substance ID: DTXSID8042636
• Metabolomics Workbench ID: 144483
• Mol file: 38129-37-2.mol

Synonyms:38129-37-2;CGP 3543/E;C12-H18-N2-O7;(1S,6R)-6-hydroxy-5-methylidene-1-[(1R,2S)-1,2,3-trihydroxy-2-methylpropyl]-2-oxa-7,9-diazabicyclo[4.2.2]decane-8,10-dione;DTXSID8042636

Chemical Property of (1S,6R)-6-hydroxy-5-methylidene-1-[(1R,2S)-1,2,3-trihydroxy-2-methylpropyl]-2-oxa-7,9-diazabicyclo[4.2.2]decane-8,10-dione

Chemical Property:

• Vapor Pressure: 1.37E-28mmHg at 25°C
• Melting Point: 188-191° (dec); mp 187-189° (dec) (Imanaka); mp 166-170° (Nakatsuka et al.)
• Refractive Index: 1.632
• Boiling Point: 786.6°C at 760 mmHg
• Flash Point: 429.5°C
• PSA: 148.35000
• Density: 1.57g/cm³
• LogP: -2.64440
• XLogP3: -2.9
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 302.11140092
• Heavy Atom Count: 21
• Complexity: 510

Purity/Quality:

98%Min ^*data from raw suppliers

BICOZAMYCIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CO)(C(C12C(=O)NC(C(=C)CCO1)(C(=O)N2)O)O)O
• Isomeric SMILES: C[C@](CO)([C@H]([C@@]12C(=O)N[C@@](C(=C)CCO1)(C(=O)N2)O)O)O
• Uses: Bicyclomycin is a polar metabolite first isolated from Streptomyces sapporonensis in 1972. The selective Gram negative profile of bicyclomycin is rare among Streptomyces metabolites. The primary site of action for bicyclomycin is thought to be the rho transcription termination factor.

Technology Process of (1S,6R)-6-hydroxy-5-methylidene-1-[(1R,2S)-1,2,3-trihydroxy-2-methylpropyl]-2-oxa-7,9-diazabicyclo[4.2.2]decane-8,10-dione

There total 42 articles about (1S,6R)-6-hydroxy-5-methylidene-1-[(1R,2S)-1,2,3-trihydroxy-2-methylpropyl]-2-oxa-7,9-diazabicyclo[4.2.2]decane-8,10-dione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

dihydrobicyclomycin 2',3'-acetonide (63777-16-2) → Aizumycin (38129-37-2)

Guidance literature:

With acetic acid; for 8h; Ambient temperature;

DOI:10.1021/jo00261a009

Reference yield: 90.0%

(1S,6R)-6-<(tert-butyldimethylsilyl)oxy>-1-<(1S,2S)-2-methyl-1,2,3-trihydroxypropyl>-5-methylene-7,9-diaza-2-oxabicyclo<4.2.2>decane-8,10-dione (95237-56-2) → Aizumycin (38129-37-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1021/jo00261a009

Reference yield:

(+)-N,N'-bis(p-methoxybenzyl)-1'-O-(trifluoroacetyl)-2',3'-O-isopropylidene-bicyclomycin (95694-73-8) → Aizumycin (38129-37-2)

Guidance literature:

With ammonium cerium(IV) nitrate; In water; acetonitrile; at 25 ℃; for 0.583333h; Yield given;

DOI:10.1021/ja00331a066

upstream raw materials:

dihydrobicyclomycin 2',3'-acetonide

(1S,6R)-6-<(tert-butyldimethylsilyl)oxy>-1-<(1S,2S)-2-methyl-1,2,3-trihydroxypropyl>-5-methylene-7,9-diaza-2-oxabicyclo<4.2.2>decane-8,10-dione

(+)-N,N'-bis(p-methoxybenzyl)-1'-O-(trifluoroacetyl)-2',3'-O-isopropylidene-bicyclomycin

L-leucine

Downstream raw materials:

(1S)-6-benzoyloxy-1-((1S,2S)-1-benzoyloxy-2-hydroxy-2-methyl-3-(Ξ)-tetrahydropyran-2-yloxy-propyl)-5-methylene-2-oxa-7,9-diaza-bicyclo[4.2.2]decane-8,10-dione

(1S)-1-((1S,2S)-1-benzoyloxy-2-hydroxy-2-methyl-3-(Ξ)-tetrahydropyran-2-yloxy-propyl)-6-hydroxy-5-methylene-2-oxa-7,9-diaza-bicyclo[4.2.2]decane-8,10-dione

(2Ξ,4S)-4-hydroxy-4-((1S)-6-hydroxy-5-methylene-8,10-dioxo-2-oxa-7,9-diaza-bicyclo[4.2.2]dec-1-yl)-3-methyl-but-2-enoic acid 4-nitro-benzyl ester

(1S)-6-hydroxy-1-((1S,2S)-1,2,3-trihydroxy-2-methyl-propyl)-2-oxa-7,9-diaza-bicyclo[4.2.2]decane-5,8,10-trione 5-phenylhydrazone

Refernces

• 1、 Yamaura, Masanori,Nakayama, Tadashi,Hashimoto, Hironobu,Shin, Chung-gi,Yoshimura, Juji,Kodama, Hisashi. "Chiral Synthesis of Bicyclomycin and Diastereomeric Stereoselectivity of the Key Aldol Condensation". . p. 6035 - 6042. Retrieved 2007/10/02.
• 2、 Williams,Armstrong,Dung. "Stereocontrolled total synthesis of (±)- and (+)-bicyclomycin: New carbon-carbon bond-forming reactions on electrophilic glycine anhydride derivatives". . p. 5748 - 5750. Retrieved 2007/10/02.